The Biggest Mistake Sales Leaders Make When Buying… | Proposify
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The Biggest Mistake Sales Leaders Make When Buying Proposal Software

What Bill Gates, Lucille Ball, and Proposify’s Customer Success team can tell you about the best way to consider, buy, implement, and use proposal software to improve your sales doc workflow’s efficiency.

8 min. read

It starts innocently enough. Sales operations says, “Let’s scale our proposal process.”

To do that, the proposal workflow needs more organization and automation. So the sales leader enters ‘proposal software’ into the search bar. They find one that makes proposals look great and comes with powerful integrations and metrics. Perfect. Purchased. Implemented.

Let’s start scaling! They bring their sales team on board. And then the team’s proposal output and sales doc quality... go down.

Gee, thanks.

What happened? This sales leader likely fell victim to one of the most common mistakes people make when buying proposal software.

The biggest proposal software misconception is...

It’s one of the most pervasive sales tool myths out there: that you can use proposal software to make your proposal process efficient.

In reality, proposal software is designed to increase your workflow’s efficiency. To paraphrase Bill Gates, technology magnifies efficiency but it also magnifies inefficiency.

Proposal software works best if there’s some kind of workflow already in place and the tool is simply there to augment, streamline, or scale it. Basically, you need a process (or at least a document) to ‘bolt’ the software onto. Here’s why:

Adding automation to an inefficient process doesn’t make it efficient

A great example of this is the candy factory episode of I Love Lucy where Lucy and Ethel are wrapping chocolates by hand.

At first, it was going well. They’re being thorough and fancy with their wrapping techniques. And then the chocolate conveyor belt speeds up. Under threat of firing if any candy makes it through unwrapped, they start hiding and throwing away candy.

Their supervisor mistakes their inefficiency for efficiency and...

Wrapping candy isn’t the same as wrapping up a deal with a proposal. But it shows how simply adding a new tool, whether it’s software or a speedy conveyor belt, without considering the implications will amplify both the strengths and weaknesses of the existing process.

Proposal software works best with a working workflow

I’ll say it again: you need something solid to bolt proposal software onto.

It’s a little like writing. It’s much easier to hone your message when you get some words down on the page and then edit them, rather than starting from a blank screen.

The workflow you have doesn’t have to be perfect. I mean, if it were, you probably wouldn’t have a pain point for proposal software to solve. The software can help you streamline a bloated or chaotic workflow but you need that starting point.

There’s no such thing as an instant fix

We’ve all been there at some point. “If I just had this one tool, everything I’m working on would automatically be better.” Or easier. Or faster. Or whatever we’re hoping for. And then we implement it and find out that it’s not a magical fix after all.

When you’re dealing with something as layered and unique as a sales process, it’s unlikely that any software solution is going to be configured perfectly right “out of the box.”

Luckily, your customer success manager (CSM) will be there to help you configure your proposal software to fit your sales team’s needs. However, they can’t do it alone. They need your input. You know your business, your processes, and your team and their needs better than anyone. And your CSM knows the software inside and out.

The questions below will get you thinking about the aspects of your sales doc workflow that will make adding proposal software into your sales tech stack a scalable success.

9 key questions to ask before you implement proposal software

Okay, so you have your workflow and you’re ready to sign-off on some proposal software. How will the software transform your creation process? What aspects will stay the same?

These are the kind of things to think about and discuss with your CSM as you implement. I’ve outlined below some of the questions you should ask to start planning for success.

Ours are a bit more specific.

Here are nine key questions, according to our customer success team:

  1. Who creates proposals now?
  2. Who will be creating proposals with the new software?
  3. What do your existing sales docs look like?
  4. What does your internal approval process look like?
  5. What’s your prospect sign-off workflow?
  6. What tech/tools are going to need to integrate with your proposal software?
  7. What account permissions and restrictions will you need?
  8. What do your proposal metrics look like now?
  9. What will success look like after using this tool for 6 months?

Who creates proposals now? Who will be creating proposals with the new software?

Who is and who will be the point people for proposal creation? What does that mean for your proposal content?

For instance, many Proposify customers once relied upon their marketing or bids departments to create proposals, but now use our app to bring that creation process “in-house” to their sales team. This transition could require some upfront work from your marketing team that you’ll want to make sure to schedule with them. They might need to update your proposal outlines for a smoother implementation or create smaller content snippets that the sales team can reuse within the app.

Less tension between departments is always a good thing.

What do your existing sales docs look like?

Are they digital? What were you using to create them—maybe Word, PDFs, or even printing out physical copies? How do you feel about them, including the design, content, flow, and ease of use?

Where do your sales docs live now? What about your content? Now’s the time to collect it all and figure out what’s working and what’s not to get ready to populate your proposal content library with your greatest hits.

What does your internal approval process look like?

What kind of deals or documents require approval from someone other than the person creating them? If so, who?

Do all docs get approved or only deals of a certain size or value? Or is an approval loop not needed?

Thinking through the approval process and building time and mechanisms for it into your sales doc workflow will help keep it flowing smoothly. That way you can avoid common bottlenecks that slow sales doc creation down, like a backlog of proposals awaiting approval piling up in a VP’s inbox.

What’s your prospect sign-off workflow?

Are you using an electronic signature tool? If not, will you move your signatures to digital? You’ll also want to consider whether the proposal software you choose has built-in digital signature capabilities or if that’s something you’ll need to integrate with a separate app.

Then consider the practical applications. If your sales reps are creating proposals, are they also signing them on behalf of your company? How will that process work? Who signs first if two signatures are required—someone from your company or the prospect?

(If you’re thinking about changing up your sign-off workflow, we have some interesting data on esignatures and proposal closed-won rates you’ll want to check out in our State of Proposals 2020 report.)

What other existing technology or tools are going to need to integrate with your proposal software?

Software integrations reduce the opportunity for error and save valuable time.

It all adds up.

Your proposal software needs to import and export data to other apps, like invoicing software and CRMs. Who owns these on your team or at your company? Do you need to get IT, accounting, or another department involved to make sure everything’s integrated correctly?

Because when apps sync up it can really pay off. Proposify customer The Payroll Company uses the Salesforce integration to keep a single source of truth for their data so they can quickly build accurate proposals and quotes.

What account permissions and restrictions will you need?

Depending on the size of your team, their technical savvy, or simply to keep the creation process streamlined, consider how you would implement access.

There might be certain content or proposal templates you want to lock down so changes can’t be made. It might also make it easier for your users if they can only see elements that they need and don’t have to search and sift through other content.

For example, Proposify power user Yellowstone Landscape has been thoughtful about how they’ve structured roles, permissions, and workspaces within proposal software. Their configuration keeps their proposals consistent and still allows their large sales team to collaborate on projects and share ideas in smaller groups.

What do your proposal metrics look like now? What will success look like after using this tool for 6 months?

Your goals might include some that are qualitative, like more consistent branding throughout your sales documents or better customer experiences for your prospects. But it’s important to also pick a couple of metrics that you can quantify, like an increase in the total number of proposals going out or faster sign-off.

This helps both you and your customer success manager evaluate the value your sales team is getting with the software and find ways to get even more out of it.

Don’t bite off more than you can chew

Adding to your sales tech stack is about so much more than just the technology. You have to think about the logistical, practical, theoretical, and even emotional impact that making changes to how people make their living brings.

You can’t plan for every possible pitfall or issue but taking a thoughtful approach from the start and letting your customer success manager in on your plan can help you avoid some of the biggest and most common mistakes.

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